It is known that the breaking of a phosphate ester bond is an important step in the destruction of chemical warfare agents such as Sarin gas and VX, in the destruction of pesticides such as chloropyrifos, and in other biological systems. Such compounds irreversibly block a serine hydroxy group in the cellular enzyme acetylcholinesterase by phosphorylation, thereby disrupting the cells' neurological function. Accordingly, substantial effort has been devoted to development of methods for decontamination of such nerve agents and pesticides. The cleavage of the P—O—C bond in such nerve agents/pesticides has been targeted as a method of decontamination. Many such methods use d-block metals such as cobalt, copper, and zinc. It is also known to destroy nerve agents by hydrolyzing them using basic solutions and/or bleach to oxidize them to less toxic inorganic phosphates and alkali. However, these solutions are caustic and should only be handled under carefully controlled conditions. Large excesses of bleach and/or bases are required for successful decontamination, and the active agent (chlorine) in bleach decreases with time. Further, bases and bleach are not selective for nerve agents, and readily undergo undesirable and potentially explosive side reactions.
Similarly, methods are known for breaking the C—O—C bond in ethers such as methyl tertiary butyl ether (MTBE) to prevent, for example, contamination of groundwater thereby. Prior art methods include cleavage by hydrogen halides, organic acids, amines/amine salts, sulfonyl halides, inorganic acid anhydrides, Lewis acid halides, Grignard reagents, and alkali metal alkyls. The modes of action of these reagents are varied, including elimination, substitution, and oxidative cleavage. Further, it is known to cleave MTBE by concentrated acid. However, concentrated acid also risks contamination of the environment, and the rate of hydrolysis is slow when dilute aqueous acid is used to avoid contamination. Biodegradation of MTBE is slow under anaerobic and aerobic conditions using conventional methodology, and certain methods such as gas phase catalytic oxidation of MTBE require high temperatures.
There is accordingly identified a need in the art for a successful deactivating/destroying agent for such toxic nerve agents as nerve gas (Sarin gas, VX, and the like) and organophosphate pesticides. Such an agent should be easily synthesized from inexpensive reagents, should be soluble in the same solvents as the nerve gases/pesticides, will preferably be selective for the nerve agents, will not readily undergo unwanted side effects upon reaction with the nerve agents, and will be substantially non-toxic.